US2026049058A1PendingUtilityA1

Crystalline forms of picolinamide fungicide compound

Assignee: CORTEVA AGRISCIENCE LLCPriority: May 31, 2022Filed: May 18, 2023Published: Feb 19, 2026
Est. expiryMay 31, 2042(~15.8 yrs left)· nominal 20-yr term from priority
B01D 9/0036B01D 9/0018C07D 213/81
47
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Claims

Abstract

The present technology relates to processes useful for making crystalline S)-1,1-bis(4-fluorophenyl)propan-2-yl (3-acetoxy-4-methoxypicolinoyl)-L-alaninate (Compound I). Processes disclosed herein describe more stable, storage compatible preparations of Compound I. Also disclosed are preparations of Compound I which have fewer (trace) impurities.

Claims

exact text as granted — not AI-modified
We claim: 
     
         1 . A process for the preparation of a crystalline compound of the formula: 
       
         
           
           
               
               
           
         
       
       the process comprising:
 distilling a mixture comprising: an aprotic organic solvent, a protic organic solvent, Compound I and seed Compound I. 
 
     
     
         2 . A process for the preparation of a crystalline compound of the formula: 
       
         
           
           
               
               
           
         
       
       the process comprising:
 a. distilling a mixture comprising: an aprotic organic solvent and Compound I; 
 b. crystallizing Compound I from step a by creating a second mixture comprising: a protic organic solvent, Compound I and seed Compound I. 
 
     
     
         3 . The process of  claim 1  wherein the aprotic organic solvent is dichloromethane. 
     
     
         4 . The process of  claim 2  wherein the amount of dichloromethane in the mixture after step a is less than 1 wt % and greater than 0.01 wt % residual dichloromethane. 
     
     
         5 . The process of  claim 2  wherein the amount of dichloromethane in the mixture after step a is less than 0.5 wt % and greater than 0.005 wt % residual dichloromethane. 
     
     
         6 . The process of  claim 2  wherein a protic organic solvent is added to the mixture in step a. 
     
     
         7 . The process of  claim 2  wherein the mixture after step a and before step b has a water content of less than 1000 ppm and greater than 50 ppm as analyzed by Karl Fisher method. 
     
     
         8 . The process of  claim 2  wherein the mixture after step a and before step b has a water content of less than 300 ppm and greater than 0.1 ppm as analyzed by Karl Fisher method. 
     
     
         9 . The process of  claim 2  wherein the amount of Compound I in the mixture after step a and before step b is less than 15 wt % and greater than 7 wt %. 
     
     
         10 . The process of  claim 2  wherein the amount of Compound I in the mixture after step a and before step b is less than 15 wt % and greater than 10 wt %. 
     
     
         11 . The process of  claim 2  wherein the amount of Compound I in the mixture after step a and before step b is less than 10 wt % and greater than 7 wt %. 
     
     
         12 . The process of  claim 2  wherein the temperature during step a is performed in a range from about 60° C. to about 10° C. 
     
     
         13 . The process of  claim 2  wherein the amount of seed Compound I is less than 50 wt % and greater than 15 wt %. 
     
     
         14 . The process of  claim 2  wherein the amount of seed Compound I is less than 10 wt % and greater than 2 wt %. 
     
     
         15 . The process of  claim 2  wherein the temperature during step b is performed in a range from about 50° C. to about 0° C. 
     
     
         16 . A crystalline polymorph of a compound of the formula: 
       
         
           
           
               
               
           
         
       
     
     
         17 . The polymorph of  claim 16  wherein the polymorph is characterized by a powder X-ray diffraction pattern having at least the 2θ reflection positions: 
       
         
           
                 
               
                     
                 
                   2θ 
                 
                     
                 
                     
                 
                 
               
                   5.97 
                 
                   10.69 
                 
                   14.71 
                 
                   16.99 
                 
                   19.41 
                 
                   23.21. 
                 
                     
                 
             
                
                
                
               
               
                
               
            
             
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         18 . The polymorph of  claim 16  wherein the polymorph is characterized by a powder X-ray diffraction pattern having at least the 2θ reflection positions: 
       
         
           
                 
               
                     
                 
                   2θ 
                 
                     
                 
                     
                 
                 
               
                   13.52 
                 
                   14.94 
                 
                   18.72 
                 
                   19.82 
                 
                   20.54 
                 
                   22.54 
                 
                   22.84.

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